Janet's Night Out


This is the follow up to Silent Night, Hot Night. To the few who expressed interest in the next chapter, I apologize for it taking so long. I'm not a very quick writer.

Special thanks to Whordinarygirl for editing the story and her helpful suggestions.


New Year's Day had come and gone. The excitement of the holidays had faded with not much on the horizon to look forward to. It was just one cold, bleak winter day after another. A cold front had blown through, leaving three more inches of snow on top of what already lay on the ground. The only warmth I found was thinking back on that evening with Zac. But even that was a distant memory, much like Christmas.

I was sitting at work, thinking of how exhilarated I had felt after that night. It was like I had discovered another piece to the puzzle that was me. I never thought it possible that I would feel this way about a man. Granted, he was a young, handsome one, but still, he was a guy. It was hard to understand but it was undeniable. So did this mean I had been gay all along and not known it? But wait, if I was becoming a woman, wouldn't it be natural to be attracted to men? Maybe I was just thinking about it too much, trying to make it either black or white. Wasn't I shaking my fist at the stereotype of what is male and female? The same could be said about sexual attraction. Why should I be so hung up on who I decided to kiss?

For the first few days after our encounter, I really believed he would call. I had convinced myself I had made that much of an impression. Every time my phone rang I would hold my breath and my heart would start beating a little faster. But it was always someone else and my spirit would crash like a duck shot out of the sky. I am not sure why I thought he would call. What did I expect after one blow job, he would dump his girlfriend for me? Sure, he said he was attracted to older women. I had that in my favor. But he had a girlfriend with a vagina, which easily trumped my age. Why would he go for a wannabe like me? Eventually, I just stopped hoping.

Then a few days after Christmas he called. I had tried so hard to put him out of mind that it took me by surprise. There was a little hesitancy in his voice. Was it because he had waited so long to call or was he questioning if it was a good idea? I decided to believe the former. He apologized for not calling sooner (point for him). He had been very busy at work, something about a server crashing. I knew enough about computers to know that was a plausible excuse but also an easy one to make up. And then he had been busy with Christmas, both preparing for and spending time with family and friends, and no doubt, his girlfriend Jennifer. He said he had thought of me often (two points) and really wanted to try to get together soon (ding, jackpot). He had to go out of town for a few days on business but when he got back, he would like to see me. I told him how nice it was to hear from him, how I understood him not calling sooner (I lied), and how I would love to get together. He said he would call soon to schedule a date and then he hung up. I did a little victory dance and thought 'best day ever'.

Fast-forward to New Year's Eve where my girlfriend Liz tried to get me to go to a party with her and her husband. I didn't feel much like partying and I definitely didn't want to be the third wheel. She assured me there would be some single guys but I didn't feel like playing The Dating Game. I had a 1000 piece jigsaw puzzle I had dug out of the closet and two bottles of wine. I was ready to greet the new year.

I was on my third glass of wine, but instead of it giving me a warm glow, I was sinking deeper into a melancholy state. I couldn't stop thinking about Zac. I cried as I thought of him, probably partying with Jennifer, and how he would kiss her at midnight. It should be me he was kissing. Why did I feel that I needed him so? Was it just my loneliness over the holidays showing through? Besides, I'm not sure any kind of relationship was right for me now. I had so many other issues I was dealing with.

I really wasn't getting anywhere on the puzzle, and I didn't feel like staying up until midnight. What's the point, it will be the beginning of a new year whether I am awake or not. I decided to go to bed.

I headed upstairs. I could have just crawled into bed. Not planning on going out, I was already dressed in my PJs. But I wanted something different tonight. I wanted to feel sexy. I stripped down, walked to the dresser and got out a long, royal blue nightgown that is one of my favorites. It has an empire waist, which makes my breasts look bigger, and a slit up the side that comes to mid-thigh. There is black lace around the neck and side opening. I always feel so feminine when I wear it. The material was cool and slick as I placed it over my head. My body quivered a little as it slid down, especially when it swept across my thighs. Since transitioning, my skin was much more sensitive.

I straightened my nightgown, pulled back the covers and climbed in. As I was drawing them up, my hand brushed across one of my nipples. A jolt of electricity ran through me. I took my fingers and began toying with it. I alternated between pinching it and running my fingers around in small circles. The silky fabric felt wonderful as it slid across my nipple. The playfulness excited me. While I cupped one hand around my breast and continued to massage it, my other hand found its way to my lap. My hand settled on the small bulge and softly began rubbing it through the satin fabric. The feeling was divine. It had been quite a while since I had played with myself. I very rarely get erections, and if I do they aren't really that hard, but it still feels good. I continued stroking the fabric, what was once cool was much warmer now. I was beginning to breathe a little heavier. I slipped into Fantasyland. I imagined Zac had snuck into my room while I was sleeping; I awoke to him touching and kissing me. He moved down my body. I felt him slowly pull up my gown. I heard him say, '"Janet, it's midnight, Happy New Year, Darling"' and then he took me in his mouth. At that moment, the feelings from my upper and lower body came together in a delightful explosion that rocked my entire being. As I moved my hand away from my dick, I felt a small wet spot on my nightgown. I smiled as I felt the warm glow...

"Janet!" I looked up and there was Bill standing in my doorway. My hand jerked up from my lap where I had been absent-mindedly stroking my thigh. I wondered how long he had been there, how long I had been lost in thought. "Leo wants to see you," he said. Leo, Mr. Farner, is the owner of the company. I work for a regional trucking company. I'm the manager over the accounting group but I have also been unofficial office manager since Jean Ann quit. I have been with the company for a long time but as a man. My coming out had not been met with many congratulations or high fives. Not that it surprised me. My company was not one of the friendliest toward transgender issues. Lots of macho men, but from the "locker room" talk I hear a lot of drivers are getting blow jobs in their rigs, and it isn't always from women. After the initial shock, Mr. Farner had been very understanding. Maybe it was because we had worked together for so long. Anyway, he had called everyone together and explained the change that was about to happen, that the company would stand behind me all the way and instructed everyone to treat me the same. I would like to say everything went smooth from that point on but of course, it didn't. There was lots of talking behind my back, and people avoiding me unless they had to deal with me. But after about six months, everyone had decided it was for real and they had mostly gotten used to it.

As I stood up, I tried to nonchalantly straighten my skirt, which, because of the under desk activities, was in a very unladylike position. I headed down the hallway to Leo's office. His door was open so I stuck my head in, "You wanted to see me?"

"Yes, come in, have a seat. We've made it to the end of another week. How are things out there in the office?"

I thought it was rather odd he called me in to ask about that. "Everything is in good shape. We got a commitment to pay on a large outstanding bill today. The check run for the 10th of the month is ready to go. I'm having a little issue with the dispatcher but I'll get it worked out."

"Good. I wanted to thank you for filling in with Jean Ann's sudden departure. It was a surprise but I understand her mother is very sick. As you probably know, I offered her a leave of absence, but because of the uncertainty of the situation, she thought it best to resign. I'm sorry it has taken me so long to begin the process of finding her replacement. The work day never has enough hours. That is why I called you in. I have some interviews scheduled for next week and I was wondering if you would mind sitting in? You probably have the best idea of the type of person we need for that job."

"I would be glad to help in any way."

"Great. Bill will be doing the interviews. I'm not expecting you to ask any questions, just get a feel for the person. Let me know what your woman's intuition tells you"

"Just let me know when and I'll make time for it."

I assumed we were finished and I was starting to get up when he said, "So Janet, how are things going, you know, with all the changes over the last year? Are things better for you now?"

His questioning caught me off guard. We hadn't really talked about my transition since I first approached him. The outward changes were obvious. I just assumed that he had the same attitude as almost everyone else; let's just not talk about it. "Things are good. Everyone here has gotten used to it, some have even accepted it."

"I'm glad to hear that but what about outside of work? I know the divorce was tough on you. Have things improved since then? Is there a support group for this kind of thing or do you have some friends to go out with?"

I wasn't sure where he was going with this questioning. I think he may have broken several HR rules in the process but that isn't something he would care about. This was a side of Leo that I hadn't seen in all the years I had worked with him, sincere and caring. Normally I would try to avoid talking about personal issues but he seemed genuinely interested. "It was very difficult in the beginning. The divorce was tough. I had hoped we could work something out but it wasn't possible. It really made me question whether it was all worth it. But now, we talk regularly on the phone and occasionally will meet for lunch." Which was usually awkward but she was trying. "I have a few of our old friends who stuck by me and I have made a few new ones. As time has passed things have improved. Sometimes I miss parts of my old life, but I am much happier now. I enjoy my new life."

"That's good to hear. I must admit, I couldn't imagine what to expect when you first told me. All I could picture was Jason in a dress. Not a very appealing image. And you probably noticed, I really had a problem calling you Janet. After all the years we have known each other, it just didn't seem right. But now, that's not an issue. I probably shouldn't say this but you are a very attractive woman and it just seems natural."

Whoa! That was really unexpected. "Thank you, Leo. You can't imagine how much it helped to be able to keep doing my job. Some days coming to work was the only thing that made my life seem normal. I realize it must have been very confusing for you and everyone else. Your support has made a big difference."

"We are celebrating my wife's 60th birthday in a few weeks. I'm planning a small party and I was wondering if you would like to come? It will just be family and a few close friends. Feel free to bring a guest."

"That sounds very nice. Let me know when and I'll see if I can make it." I stood up, "If that's all I'll get back to work. I would like to make some progress on the quarterly reports before the end of the day."

"That's it. I would definitely like to see those reports next week. Once again, thanks for helping to keep this place running Janet."

As I walked back to my office, I thought about what had just happened. It was all quite unbelievable. Leo had called me a woman twice and when he referred to my old male persona, it was like Jason was a totally different entity. Then there was the invitation to socialize with his family, me, a transgender woman. I flashed back to the tag line of an old cigarette commercial, 'you've come a long way baby'.

The rest of the day was spent at my desk. The clock ticked closer to 5 o'clock. The work day was almost over and I couldn't be happier. Thinking about Zac had just made me feel lonelier and I just wanted to go home. It had been almost two weeks since I had heard from him. I guess he had second thoughts about that date. Melissa, one of the younger women in the office, stuck her head in my door. "Several of us girls are going to grab a drink after work, you know TGIF. We were wondering if you would like to join us."

My initial thought was to decline. I didn't feel like I would be much company. "Thanks, but I don't," I paused in mid-sentence. It occurred to me that this is just what I needed, a drink and some female company. "Actually, that sounds great. Where are you going?"

"Someplace close. We were thinking The Lion's Den," she said.

Our office is on the south side of the city, near a large, urban university. And wherever you find college students, you will find bars. I had been there for lunch a few times. It was a nice, casual place. "That sounds good. Are you leaving right away?"

"As soon as the big hand hits twelve," Melissa said and then giggled.

"Okay. I need to finish a few things, so I will meet you there." She turned and scurried off. I had some last minute paperwork to deal with before I could leave. It was nice that she had asked me. The younger women in the office seemed more accepting of me than the women more my age.

The bar was a short drive from the office. I walked in and surveyed the crowd, looking for my group. I noticed I got several odd stares. I'm used to that. With makeup and my hair done right, I'm passable and somewhat attractive. But I still have a bit of a mannish look. So, there is always someone with the 'is that a' look. But by this point in my transition, I really don't care what others think. I couldn't or I would never leave the house.

I saw them sitting at a table. There was Melissa, Leah, and Carrie. They were all women who work for me and all about the same age, mid-20s. Both Leah and Carrie were married but no kids. Melissa isn't but I think she has a boyfriend. As I approached the table, Melissa saw me and waved. They were all excited about something, probably just that it was the weekend.

As I reached the table the waiter came up with drinks. "I have two margaritas and a Sprite." He sat the soda in front of Carrie. He looked at me, "What may I get for you?"

"I'll have a glass of Zinfandel." As much as I wanted a margarita, I needed to maintain my composure. I was their boss and I didn't need stories of me partying wildly getting back to the office. "What, no margarita for you Carrie?"

"Tell her," exclaimed Melissa

"Yes, tell her," Leah chimed in

Carrie was smiling ear to ear, almost bursting as she waited to tell me. "I'm pregnant! I just found out today!"

"Oh, that's wonderful." Obviously, this was the discussion that was going on before I got there. I didn't know anything about her home life but she seemed extremely happy so I was happy for her. Anyway, that became the main topic for a while. Of course, we talked some about work. I tried to remain generic on the subject. I didn't want to let something slip that I shouldn't. And, of course, they had questions about how things were with me and my situation. I'm sure it was quite novel for them to know someone transitioning.

Leah asked, "So is there a boyfriend you are hiding from us?"

The woman in me wanted to tell them all about Zac, about the special evening, and about plans to meet again. But I didn't need that spread all around the office. Besides, I don't know if there was much to tell except I gave a guy a blow job and that appeared to be the end of the story.

Then Melissa said, "What about a girlfriend?" And they all giggled.

"I'm not sure if the guy I have chained in my basement counts as a boyfriend," I said with a serious look on my face. I paused long enough for them to think about what I had said. "Just kidding, I have no romantic entanglements at this time. It is just me and my cat, and we're just good friends"

I was on my second glass of wine and thinking about leaving. I was gazing at the door when in walked a vision from my high school dreams. She was wearing black leather boots that came up to her knees. I think her jeans must have been painted on because they couldn't have been any tighter. Her coat was open and I could see the fabric of her top was stretched quite tight. She had straight black hair that came just below her shoulders, a big pair of dark sunglasses and full, kissable lips. I looked around and noticed she was getting looks from most of the male patrons. After a quick glance around, she headed straight for our table.

Melissa looked up and saw her. "Wow, you really did make it! Everyone this is my friend Michelle. Michelle, this is Leah, Carrie, and Janet," she pointed to us respectively.

"Glad to meet you all," she said as she pulled up a chair. Turning to look at me, "Janet, I've heard so much about you."

It made me wonder what Melissa had told her. "Me? I hope it was all good. Not like what a horrible boss I am."

Before Michelle could answer, Melissa jumped in, "Relax. It was all good. Michelle and I grew up together. We first met in elementary school and we've been together since. We are almost like sisters. So we kind of tell each other everything." And with that, she began telling stories of things they had done over the years. Michelle would chime in occasionally, usually to tell her version.

Carrie was the first to leave. She said she hadn't told her husband the news. She had found out late in the day and didn't want to tell him over the phone.

Leah seized the opportunity to bolt. She had plans to go see a movie and she needed to get home.

My earlier thought of leaving had disappeared. Melissa continued talking about their exploits and they would laugh at the inside jokes. For some reason, Michelle seemed very interested in me. When Melissa would pause to take a drink, she would take the opportunity to ask something about me or my transition. Melissa's phone rang.

"'Hi, babe... I'm out with some of the girls... I told you that's where I was going. I can't help it you never listen to me... Okay, I'll be home soon.' That was David. It seems we were supposed to go to his friend's house this evening."

Michelle had a rather perturbed look on her face. "Melissa, I keep telling you, you can do better."

"Michelle, stop. I know David can be demanding but he can also be sweet. I better get going. You two have fun." Melissa had a sullen look until that last sentence. She smiled and walked away.

After Melissa was gone, Michelle said, "He is such a jerk. But she doesn't see it. She thinks that is just what guys are like and she doesn't want to be without one."

I really didn't want to get in the middle of their dispute. "I really don't know much about the situation. I do know that sometimes we desire a relationship, good or bad because we don't want to be alone. We buy into the line that we have to have our soul mate to be happy."

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byJanetHarper© 6 comments/ 23968 views/ 10 favorites

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